A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin. Issue 26 (28th June 2018)

• Record Type: Journal Article
• Authors: Haut, Franz-Lucas; Speck, Klaus; Wildermuth, Raphael; Möller, Kristof; Mayer, Peter; Magauer, Thomas
• Is Part Of: Tetrahedron. Volume 74:Issue 26(2018)
• Page Start: 3348
• Page End: 3357
• Publication Date: 2018-06-28
• Subjects: Meroterpenoids -- Natural product synthesis -- Diels–Alder cycloaddition -- Negishi cross-coupling -- Wagner–Meerwein rearrangement; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.048
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We present a full account on the development of the total synthesis of the antiviral meroterpenoid (+)-stachyflin. The decalin subunit is rapidly accessed by an exo -selective Diels–Alder reaction, whereas the isonindolinone was synthesized via a highly efficient and practical de novo route starting from dimedone. A challenging sp 2 –sp 3 Negishi cross-coupling reaction enabled construction of the crucial C15–C16 bond that connects the arene with the decalin subunit. For the final installation of the cis -decalin framework, a Lewis acid-catalyzed cyclization was applied. Graphical abstract: Image 1